Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
US5225584A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 3, 1991 |
| Grant date | Jul 6, 1993 |
| Priority date | — |
| Expiry date | Apr 3, 2011 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2603/74
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel synthesis of compounds having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R.sup.3 is a C.sub.1 -C.sub.20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula: EQU (R.sup.1 O).sub.3 P wherein R.sup.1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula: EQU R.sup.3 OH wherein R.sup.3 is as defined above, to produce a 1-alkoxy-1-arylmethane phosphonate ester of the formula: ##STR2## reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula: EQU T.dbd.O wherein T is as defined above, to produce an enol ether of the formula: ##STR3## then oxygenating the double bond in the enol ether to give the corresponding 1,2-dioxetane compound.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.